@jhsrennie,
You could try the following approach:
Open your RTF in Word and style every chapter heading with one of Word's built-in Heading styles 'Heading 1' or 'Heading 2'. Save the RTF and try again.
If you set the --chapter-mark option to "pagebreak" then Calibre's default --chapter option should put pagebreaks before each chapter.
I would post a sample CLI command for you but I'm afraid I always use the Calibre GUI.
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